Literature DB >> 19006314

A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Qiuzhe Xie1, Richard W Denton, Kathlyn A Parker.   

Abstract

A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short, high yield, and convenient route to trisubstituted Z-vinyl iodides, useful intermediates for the preparation of polypropionate antibiotics.

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Year:  2008        PMID： 19006314      PMCID： PMC2765515          DOI： 10.1021/ol802063h

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  26 in total

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Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

2.  A convergent total synthesis of hemibrevetoxin B.

Authors:  Armen Zakarian; Alexandre Batch; Robert A Holton
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419

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Authors:  Amos B Smith; B Scott Freeze
Journal:  Tetrahedron       Date:  2007-01-07       Impact factor: 2.457

4.  Total synthesis of (-)-mucocin.

Authors:  Michael T Crimmins; Yan Zhang; Frank A Diaz
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

5.  alpha-Oxygenated crotyltitanium and dyotropic rearrangement in the total synthesis of discodermolide.

Authors:  Elsa de Lemos; François-Hugues Porée; Alain Commerçon; Jean-François Betzer; Ange Pancrazi; Janick Ardisson
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Asymmetric allylboration and ring closing alkene metathesis: a novel strategy for the synthesis of glycosphingolipids.

Authors:  A G Barrett; J C Beall; D C Braddock; K Flack; V C Gibson; M M Salter
Journal:  J Org Chem       Date:  2000-10-06       Impact factor: 4.354

7.  Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

Authors:  Guangwu Chen; John Schmieg; Moriya Tsuji; Richard W Franck
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

8.  Scalable, catalytic asymmetric synthesis of syn, anti stereotriad building blocks for polypropionate antibiotics.

Authors:  Kathlyn A Parker; Huanyan Cao
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

9.  Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes.

Authors:  Reagan L Miller; Sarah V Maifeld; Daesung Lee
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

10.  Synthesis of +-dihydro-epi-deoxyarteannuin B.

Authors:  Gregory B Dudley; Douglas A Engel; Ion Ghiviriga; Hubert Lam; Kevin W C Poon; Jeananne A Singletary
Journal:  Org Lett       Date:  2007-06-21       Impact factor: 6.005
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  4 in total

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Journal:  Org Lett       Date:  2011-06-16       Impact factor: 6.005

2.  Functional group compatibility. Propargyl alcohol reduction in the presence of a vinyl iodide.

Authors:  Richard W Denton; Kathlyn A Parker
Journal:  Org Lett       Date:  2009-07-02       Impact factor: 6.005

3.  Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane.

Authors:  James R Vyvyan; Courtney A Engles; Scott L Bray; Erik D Wold; Christopher L Porter; Mikhail O Konev
Journal:  Beilstein J Org Chem       Date:  2017-10-11       Impact factor: 2.883

4.  Collective Total Synthesis of Casbane Diterpenes: One Strategy, Multiple Targets.

Authors:  Lorenz E Löffler; Conny Wirtz; Alois Fürstner
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-28       Impact factor: 15.336
  4 in total

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